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Diastereoselective reactions of 1,1,1-trichloro(trifluoro)-3-nitrobut-2-enes with 2-morpholinoalk-1-enes

Vladislav Yurievich Korotaev 1
Vladislav Yurievich Korotaev
, 
Alexey Yurievich Barkov 1
Alexey Yurievich Barkov
, 
Pavel Alexandrovich Slepukhin 2
Pavel Alexandrovich Slepukhin
, 
Mikhail Isaakovich Kodess 2
Mikhail Isaakovich Kodess
, 
Vyacheslav Yakovlevich Sosnovskikh 1
Vyacheslav Yakovlevich Sosnovskikh
10.1016/j.mencom.2011.03.020
Published 2011-03-10
Communication , Volume 21, Issue 2, 112-114
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Korotaev V. Y. et al. Diastereoselective reactions of 1,1,1-trichloro(trifluoro)-3-nitrobut-2-enes with 2-morpholinoalk-1-enes // Mendeleev Communications. 2011. Vol. 21. No. 2. pp. 112-114.
GOST all authors (up to 50) Copy
Korotaev V. Y., Barkov A. Y., Slepukhin P. A., Kodess M. I., Sosnovskikh V. Y. Diastereoselective reactions of 1,1,1-trichloro(trifluoro)-3-nitrobut-2-enes with 2-morpholinoalk-1-enes // Mendeleev Communications. 2011. Vol. 21. No. 2. pp. 112-114.
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TY - JOUR
DO - 10.1016/j.mencom.2011.03.020
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.03.020
TI - Diastereoselective reactions of 1,1,1-trichloro(trifluoro)-3-nitrobut-2-enes with 2-morpholinoalk-1-enes
T2 - Mendeleev Communications
AU - Korotaev, Vladislav Yurievich
AU - Barkov, Alexey Yurievich
AU - Slepukhin, Pavel Alexandrovich
AU - Kodess, Mikhail Isaakovich
AU - Sosnovskikh, Vyacheslav Yakovlevich
PY - 2011
DA - 2011/03/10
PB - Mendeleev Communications
SP - 112-114
IS - 2
VL - 21
ER -
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@article{2011_Korotaev,
author = {Vladislav Yurievich Korotaev and Alexey Yurievich Barkov and Pavel Alexandrovich Slepukhin and Mikhail Isaakovich Kodess and Vyacheslav Yakovlevich Sosnovskikh},
title = {Diastereoselective reactions of 1,1,1-trichloro(trifluoro)-3-nitrobut-2-enes with 2-morpholinoalk-1-enes},
journal = {Mendeleev Communications},
year = {2011},
volume = {21},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.03.020},
number = {2},
pages = {112--114},
doi = {10.1016/j.mencom.2011.03.020}
}
MLA
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MLA Copy
Korotaev, Vladislav Yurievich, et al. “Diastereoselective reactions of 1,1,1-trichloro(trifluoro)-3-nitrobut-2-enes with 2-morpholinoalk-1-enes.” Mendeleev Communications, vol. 21, no. 2, Mar. 2011, pp. 112-114. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.03.020.

Abstract

Reactions of (E)-1,1,1-trichloro(trifluoro)-3-nitrobut-2-enes with 3,3-dimethyl-2-morpholinobutene in benzene give (4R*,6R*)-6-tert-butyl-3-methyl-6-morpholino-4-trihalomethyl-5,6-dihydro-4H-1,2-oxazine 2-oxides. In a dichloromethane solution, these cyclic nitronates undergo diastereoselective ring opening to produce nitroalkylated anti-CCl3- and syn-CF3-enamines, which are hydrolysed with dilute HCl to afford the respective anti-CCl3- and syn-CF3-g-nitroketones.

References

1.
10.1016/j.mencom.2011.03.020_bib0005_1
Ono
The Nitro Group in Organic Synthesis, 2001
2.
Oxoalkylation of carbonyl compounds with conjugated nitro olefins
Yoshikoshi A., Miyashita M.
Accounts of Chemical Research, 1985
6.
10.1016/j.mencom.2011.03.020_bib0015_2
Risaliti
Tetrahedron, 1966, 24, 1889
7.
Mononitroalkylations of Butane-2,3-dione
Pitacco G., Pizzioli A., Valentin E.
Synthesis, 1996
8.
Reaction of Enamines with Nitro Olefins1
Kuehne M.E., Foley L.
Journal of Organic Chemistry, 1965
9.
Enamine Chemistry. IV. Cycloaddition Reactions of Enamines Derived from Aldehydes and Acyclic Ketones1,2
Brannock K.C., Bell A., Burpitt R.D., Kelly C.A.
Journal of Organic Chemistry, 1964
11.
Cyclic nitronic esters
Nielsen A.T., Archibald T.G.
Tetrahedron, 1970
13.
α-Nitrostyrene. First reactions with enamines
Bradamante P., Pitacco G., Risaliti A., Valentin E.
Tetrahedron Letters, 1982
15.
10.1002/(SICI)1522-2675(19991110)82:11<1829::AID-HLCA1829>3.0.CO;2-#
16.
New C−C Coupling Reaction of Cyclic Nitronates with Carbon Nucleophiles. Umpolung of the Conventional Reactivity of Nitronates
Smirnov V.O., Ioffe S.L., Tishkov A.A., Khomutova Y.A., Nesterov I.D., Antipin M.Y., Smit W.A., Tartakovsky V.A.
Journal of Organic Chemistry, 2004
17.
10.1016/j.mencom.2011.03.020_bib0030_4
Klenov
Synthesis, 2004
18.
10.1016/j.mencom.2011.03.020_bib0035
Aizikovich
Zh. Org. Khim., 1998
19.
New functionalized, differently fluorinated building-blocks via Michael addition to γ-fluoro-α-nitroalkenes
Molteni M., Consonni R., Giovenzana T., Malpezzi L., Zanda M.
Journal of Fluorine Chemistry, 2006
20.
V. Yu. Korotaev, A.Yu. Barkov, P. A. Slepukhin and V. Ya. Sosnovskikh, Izv. Akad. Nauk, Ser. Khim., in press.
21.
1-nitro-1-phenylpropene
Asaro F., Pitacco G., Valentin E.
Tetrahedron, 1987
24.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007